A Simple Synthesis of α-Ylidene γ-Lactones from γ-Trimethylsiloxy Nitriles
- 1 August 1979
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 52 (8), 2389-2393
- https://doi.org/10.1246/bcsj.52.2389
Abstract
α-Cyano carbanions which are generated from γ-trimethylsiloxy nitriles have been found to react with aldehydes to give α-(1-hydroxyalkyl)-γ-trimethylsiloxy nitriles (6). α-Ylidene γ-lactones (5) are derived from 6 in two steps; hydrolytic lactonization to α-(1-hydroxyalkyl) γ-lactones and dehydration. The stereochemistry of the lactones 5 with one exception have been found to be of the E form on the basis of the NMR spectra.Keywords
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